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EP4239005A3 - New formulation methodology for distortional thermosets - Google Patents

New formulation methodology for distortional thermosets Download PDF

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Publication number
EP4239005A3
EP4239005A3 EP23183604.0A EP23183604A EP4239005A3 EP 4239005 A3 EP4239005 A3 EP 4239005A3 EP 23183604 A EP23183604 A EP 23183604A EP 4239005 A3 EP4239005 A3 EP 4239005A3
Authority
EP
European Patent Office
Prior art keywords
distortional
new formulation
thermosets
distortional thermosets
formulation methodology
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP23183604.0A
Other languages
German (de)
French (fr)
Other versions
EP4239005B1 (en
EP4239005A2 (en
Inventor
Stephen Christensen
Samuel J. Tucker
Jeffrey S. Wiggins
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boeing Co
Original Assignee
Boeing Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Boeing Co filed Critical Boeing Co
Publication of EP4239005A2 publication Critical patent/EP4239005A2/en
Publication of EP4239005A3 publication Critical patent/EP4239005A3/en
Application granted granted Critical
Publication of EP4239005B1 publication Critical patent/EP4239005B1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5033—Amines aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5026—Amines cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/56—Amines together with other curing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/66—Mercaptans
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/246—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using polymer based synthetic fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/06—Elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/14—Glass
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C08J2377/06—Polyamides derived from polyamines and polycarboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Reinforced Plastic Materials (AREA)

Abstract

Methods and formulations for distortional thermosets are disclosed that display enhanced composite mechanical performances and robust sorption resistance. The composition includes an epoxy resin of formula (I): and a diamine curing agent. The resultant distortional thermoset compositions possess superior out-life requirements and advantageous reaction kinetics for preparing prepreg compositions and materials.
EP23183604.0A 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets Active EP4239005B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US13/963,745 US9309353B2 (en) 2013-08-09 2013-08-09 Formulation methodology for distortional thermosets
EP14180355.1A EP2842981B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets
EP19201804.2A EP3613790B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets

Related Parent Applications (3)

Application Number Title Priority Date Filing Date
EP14180355.1A Division EP2842981B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets
EP19201804.2A Division-Into EP3613790B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets
EP19201804.2A Division EP3613790B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets

Publications (3)

Publication Number Publication Date
EP4239005A2 EP4239005A2 (en) 2023-09-06
EP4239005A3 true EP4239005A3 (en) 2023-10-11
EP4239005B1 EP4239005B1 (en) 2025-06-04

Family

ID=51302915

Family Applications (3)

Application Number Title Priority Date Filing Date
EP19201804.2A Active EP3613790B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets
EP14180355.1A Active EP2842981B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets
EP23183604.0A Active EP4239005B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets

Family Applications Before (2)

Application Number Title Priority Date Filing Date
EP19201804.2A Active EP3613790B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets
EP14180355.1A Active EP2842981B1 (en) 2013-08-09 2014-08-08 New formulation methodology for distortional thermosets

Country Status (3)

Country Link
US (4) US9309353B2 (en)
EP (3) EP3613790B1 (en)
AU (4) AU2014204474B2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9309353B2 (en) * 2013-08-09 2016-04-12 The Boeing Company Formulation methodology for distortional thermosets
EP3487904A4 (en) 2016-07-25 2020-06-10 The Boeing Company EPOXY RESIN
CA3031544C (en) * 2016-07-25 2024-04-23 The Boeing Company Epoxy resin

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB789392A (en) * 1955-05-26 1958-01-22 Bakelite Ltd Improvements in or relating to epoxide resins
US2986550A (en) * 1955-05-26 1961-05-30 Bakelite Ltd Polynuclear epoxide resin
US20070149725A1 (en) * 2005-12-22 2007-06-28 The Boeing Company Distortional composite matrix
WO2012064662A1 (en) * 2010-11-08 2012-05-18 Toray Industries, Inc. Epoxy resin composition for fiber reinforced composite material, prepreg, and fiber reinforced composite material

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US3286836A (en) 1965-06-30 1966-11-22 Monte Amiata Societa Mineraria Lined flask for mercury
US3406488A (en) 1965-09-23 1968-10-22 Minnesota Mining & Mfg Abrasive flap wheel
DE4040471A1 (en) * 1990-08-01 1992-02-06 Bayer Ag CURABLE MIXTURES FOR THE PRODUCTION OF EPOXY NETWORKS, METHOD FOR THE PRODUCTION AND USE THEREOF
US5180627A (en) * 1990-11-30 1993-01-19 Ube Industries, Ltd. Heat resistant adhesive composition
US5360840A (en) * 1992-12-29 1994-11-01 Hercules Incorporated Epoxy resin compositions with improved storage stability
US5532331A (en) 1993-06-24 1996-07-02 The Dow Chemical Company Thiodiphenol copolycarbonates and their use as components of multilayered polymeric reflective bodies
US6117510A (en) * 1996-07-30 2000-09-12 Ube Industries, Ltd. Adhesive-applied tape
GB0117155D0 (en) 2001-07-13 2001-09-05 Coates Electrographics Ltd Improvement in or relating to photocurable resist inks
KR20090107046A (en) 2007-02-07 2009-10-12 미쓰비시 가가꾸 가부시키가이샤 Coating liquid for electrophotographic photosensitive members, electrophotographic photosensitive member, electrophotographic photosensitive member cartridge
DE102009028100A1 (en) 2009-07-29 2011-02-03 Henkel Ag & Co. Kgaa Impact-modified epoxy resin-based composition
US9309353B2 (en) * 2013-08-09 2016-04-12 The Boeing Company Formulation methodology for distortional thermosets

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB789392A (en) * 1955-05-26 1958-01-22 Bakelite Ltd Improvements in or relating to epoxide resins
US2986550A (en) * 1955-05-26 1961-05-30 Bakelite Ltd Polynuclear epoxide resin
US20070149725A1 (en) * 2005-12-22 2007-06-28 The Boeing Company Distortional composite matrix
WO2012064662A1 (en) * 2010-11-08 2012-05-18 Toray Industries, Inc. Epoxy resin composition for fiber reinforced composite material, prepreg, and fiber reinforced composite material

Also Published As

Publication number Publication date
AU2017208260B2 (en) 2018-05-31
EP2842981B1 (en) 2019-11-06
AU2018220096B2 (en) 2019-12-19
EP3613790B1 (en) 2023-11-01
EP3613790A1 (en) 2020-02-26
US20150045505A1 (en) 2015-02-12
AU2018201024B2 (en) 2018-05-31
US9938372B2 (en) 2018-04-10
US10619002B2 (en) 2020-04-14
AU2018201024A1 (en) 2018-03-01
AU2018220096A1 (en) 2018-09-13
EP4239005B1 (en) 2025-06-04
US20180230262A1 (en) 2018-08-16
EP4239005A2 (en) 2023-09-06
US20170101503A1 (en) 2017-04-13
US20160194437A1 (en) 2016-07-07
US9556306B2 (en) 2017-01-31
AU2017208260A1 (en) 2017-08-10
US9309353B2 (en) 2016-04-12
AU2014204474A1 (en) 2015-02-26
AU2014204474B2 (en) 2017-07-13
EP2842981A1 (en) 2015-03-04

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